CN107635966B - Compound and organic electronic device comprising same - Google Patents
Compound and organic electronic device comprising same Download PDFInfo
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- CN107635966B CN107635966B CN201680034119.8A CN201680034119A CN107635966B CN 107635966 B CN107635966 B CN 107635966B CN 201680034119 A CN201680034119 A CN 201680034119A CN 107635966 B CN107635966 B CN 107635966B
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 124
- -1 benzofluorenyl group Chemical group 0.000 claims description 74
- 239000011368 organic material Substances 0.000 claims description 66
- 239000000126 substance Substances 0.000 claims description 63
- 125000003118 aryl group Chemical group 0.000 claims description 48
- 238000002347 injection Methods 0.000 claims description 47
- 239000007924 injection Substances 0.000 claims description 47
- 230000032258 transport Effects 0.000 claims description 42
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
- 230000000903 blocking effect Effects 0.000 claims description 16
- 230000005525 hole transport Effects 0.000 claims description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 125000001072 heteroaryl group Chemical group 0.000 claims description 13
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 12
- 125000003367 polycyclic group Chemical group 0.000 claims description 12
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- 125000002950 monocyclic group Chemical group 0.000 claims description 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 8
- 229910052805 deuterium Inorganic materials 0.000 claims description 8
- 150000002431 hydrogen Chemical class 0.000 claims description 8
- 125000001624 naphthyl group Chemical group 0.000 claims description 7
- 125000001725 pyrenyl group Chemical group 0.000 claims description 7
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 7
- 125000000732 arylene group Chemical group 0.000 claims description 6
- 239000004305 biphenyl Substances 0.000 claims description 6
- 235000010290 biphenyl Nutrition 0.000 claims description 6
- 125000005561 phenanthryl group Chemical group 0.000 claims description 6
- 125000004076 pyridyl group Chemical group 0.000 claims description 5
- 125000004957 naphthylene group Chemical group 0.000 claims description 4
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 4
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 claims description 2
- 125000005549 heteroarylene group Chemical group 0.000 claims description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims 2
- 239000010410 layer Substances 0.000 description 219
- 238000002360 preparation method Methods 0.000 description 42
- 239000000463 material Substances 0.000 description 41
- 229940125904 compound 1 Drugs 0.000 description 36
- 125000001424 substituent group Chemical group 0.000 description 34
- 238000003786 synthesis reaction Methods 0.000 description 23
- 238000002474 experimental method Methods 0.000 description 19
- 238000000034 method Methods 0.000 description 14
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 11
- 239000000758 substrate Substances 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- 238000000151 deposition Methods 0.000 description 7
- 239000002019 doping agent Substances 0.000 description 7
- 229910052751 metal Inorganic materials 0.000 description 7
- 239000002184 metal Substances 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- 229910052782 aluminium Inorganic materials 0.000 description 6
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 6
- 125000000623 heterocyclic group Chemical group 0.000 description 6
- OPFJDXRVMFKJJO-ZHHKINOHSA-N N-{[3-(2-benzamido-4-methyl-1,3-thiazol-5-yl)-pyrazol-5-yl]carbonyl}-G-dR-G-dD-dD-dD-NH2 Chemical compound S1C(C=2NN=C(C=2)C(=O)NCC(=O)N[C@H](CCCN=C(N)N)C(=O)NCC(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(N)=O)=C(C)N=C1NC(=O)C1=CC=CC=C1 OPFJDXRVMFKJJO-ZHHKINOHSA-N 0.000 description 5
- 150000004982 aromatic amines Chemical class 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 229940126086 compound 21 Drugs 0.000 description 5
- 125000004122 cyclic group Chemical group 0.000 description 5
- 239000012153 distilled water Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000007774 positive electrode material Substances 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 229940126657 Compound 17 Drugs 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- PSLUFJFHTBIXMW-WYEYVKMPSA-N [(3r,4ar,5s,6s,6as,10s,10ar,10bs)-3-ethenyl-10,10b-dihydroxy-3,4a,7,7,10a-pentamethyl-1-oxo-6-(2-pyridin-2-ylethylcarbamoyloxy)-5,6,6a,8,9,10-hexahydro-2h-benzo[f]chromen-5-yl] acetate Chemical compound O([C@@H]1[C@@H]([C@]2(O[C@](C)(CC(=O)[C@]2(O)[C@@]2(C)[C@@H](O)CCC(C)(C)[C@@H]21)C=C)C)OC(=O)C)C(=O)NCCC1=CC=CC=N1 PSLUFJFHTBIXMW-WYEYVKMPSA-N 0.000 description 4
- 125000001769 aryl amino group Chemical group 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000004770 highest occupied molecular orbital Methods 0.000 description 4
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Inorganic materials [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 4
- 239000007773 negative electrode material Substances 0.000 description 4
- 125000002560 nitrile group Chemical group 0.000 description 4
- 125000000714 pyrimidinyl group Chemical group 0.000 description 4
- 125000004306 triazinyl group Chemical group 0.000 description 4
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 3
- WWTBZEKOSBFBEM-SPWPXUSOSA-N (2s)-2-[[2-benzyl-3-[hydroxy-[(1r)-2-phenyl-1-(phenylmethoxycarbonylamino)ethyl]phosphoryl]propanoyl]amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound N([C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)O)C(=O)C(CP(O)(=O)[C@H](CC=1C=CC=CC=1)NC(=O)OCC=1C=CC=CC=1)CC1=CC=CC=C1 WWTBZEKOSBFBEM-SPWPXUSOSA-N 0.000 description 3
- UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 description 3
- FMKGJQHNYMWDFJ-CVEARBPZSA-N 2-[[4-(2,2-difluoropropoxy)pyrimidin-5-yl]methylamino]-4-[[(1R,4S)-4-hydroxy-3,3-dimethylcyclohexyl]amino]pyrimidine-5-carbonitrile Chemical compound FC(COC1=NC=NC=C1CNC1=NC=C(C(=N1)N[C@H]1CC([C@H](CC1)O)(C)C)C#N)(C)F FMKGJQHNYMWDFJ-CVEARBPZSA-N 0.000 description 3
- QBWKPGNFQQJGFY-QLFBSQMISA-N 3-[(1r)-1-[(2r,6s)-2,6-dimethylmorpholin-4-yl]ethyl]-n-[6-methyl-3-(1h-pyrazol-4-yl)imidazo[1,2-a]pyrazin-8-yl]-1,2-thiazol-5-amine Chemical compound N1([C@H](C)C2=NSC(NC=3C4=NC=C(N4C=C(C)N=3)C3=CNN=C3)=C2)C[C@H](C)O[C@H](C)C1 QBWKPGNFQQJGFY-QLFBSQMISA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 229940126639 Compound 33 Drugs 0.000 description 3
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
- PNUZDKCDAWUEGK-CYZMBNFOSA-N Sitafloxacin Chemical compound C([C@H]1N)N(C=2C(=C3C(C(C(C(O)=O)=CN3[C@H]3[C@H](C3)F)=O)=CC=2F)Cl)CC11CC1 PNUZDKCDAWUEGK-CYZMBNFOSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- LNUFLCYMSVYYNW-ZPJMAFJPSA-N [(2r,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[[(3s,5s,8r,9s,10s,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-disulfo Chemical compound O([C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1C[C@@H]2CC[C@H]3[C@@H]4CC[C@@H]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)[C@H](C)CCCC(C)C)[C@H]1O[C@H](COS(O)(=O)=O)[C@@H](OS(O)(=O)=O)[C@H](OS(O)(=O)=O)[C@H]1OS(O)(=O)=O LNUFLCYMSVYYNW-ZPJMAFJPSA-N 0.000 description 3
- SMNRFWMNPDABKZ-WVALLCKVSA-N [[(2R,3S,4R,5S)-5-(2,6-dioxo-3H-pyridin-3-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [[[(2R,3S,4S,5R,6R)-4-fluoro-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl] hydrogen phosphate Chemical compound OC[C@H]1O[C@H](OP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)C2C=CC(=O)NC2=O)[C@H](O)[C@@H](F)[C@@H]1O SMNRFWMNPDABKZ-WVALLCKVSA-N 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
- 229940125797 compound 12 Drugs 0.000 description 3
- 229940126208 compound 22 Drugs 0.000 description 3
- 229940125846 compound 25 Drugs 0.000 description 3
- 229940127113 compound 57 Drugs 0.000 description 3
- 229920001940 conductive polymer Polymers 0.000 description 3
- 230000021615 conjugation Effects 0.000 description 3
- 239000000470 constituent Substances 0.000 description 3
- 230000008021 deposition Effects 0.000 description 3
- 229910052733 gallium Inorganic materials 0.000 description 3
- 150000002430 hydrocarbons Chemical group 0.000 description 3
- IMKMFBIYHXBKRX-UHFFFAOYSA-M lithium;quinoline-2-carboxylate Chemical compound [Li+].C1=CC=CC2=NC(C(=O)[O-])=CC=C21 IMKMFBIYHXBKRX-UHFFFAOYSA-M 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 229910052709 silver Inorganic materials 0.000 description 3
- 239000004332 silver Substances 0.000 description 3
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- APHLSUBLNQBFTM-UHFFFAOYSA-N (2-aminophenyl)-(4-chlorophenyl)methanone Chemical compound NC1=CC=CC=C1C(=O)C1=CC=C(Cl)C=C1 APHLSUBLNQBFTM-UHFFFAOYSA-N 0.000 description 2
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 2
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
- QENGPZGAWFQWCZ-UHFFFAOYSA-N 3-Methylthiophene Chemical compound CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 125000006267 biphenyl group Chemical group 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000010406 cathode material Substances 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 229940125782 compound 2 Drugs 0.000 description 2
- 229940126214 compound 3 Drugs 0.000 description 2
- 229940125898 compound 5 Drugs 0.000 description 2
- 150000004696 coordination complex Chemical class 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 150000002219 fluoranthenes Chemical class 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 150000002825 nitriles Chemical group 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- 125000001715 oxadiazolyl group Chemical group 0.000 description 2
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 125000005562 phenanthrylene group Chemical group 0.000 description 2
- 238000005240 physical vapour deposition Methods 0.000 description 2
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 2
- 229920000767 polyaniline Polymers 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229910052711 selenium Inorganic materials 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
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- 239000010409 thin film Substances 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
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Abstract
The present description relates to compounds and organic electronic devices comprising the same.
Description
Technical Field
The present invention claims priority and benefit of korean patent application No. 10-2015-.
The present description relates to compounds and organic electronic devices comprising the same.
Background
Representative examples of organic electronic devices include organic light emitting devices. In general, the organic light emitting phenomenon refers to a phenomenon of converting electric energy into light energy by using an organic material. An organic light emitting device using an organic light emitting phenomenon generally has a structure including a positive electrode, a negative electrode, and an organic material layer interposed therebetween. Here, the organic material layer may have a multi-layered structure composed of different materials in many cases to improve efficiency and stability of the organic light emitting device, for example, the organic material layer may be composed of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like. In the structure of the organic light emitting device, if a voltage is applied between two electrodes, holes are injected from a positive electrode into an organic material layer and electrons are injected from a negative electrode into the organic material layer, excitons are formed when the injected holes and electrons meet each other, and light is emitted when the excitons fall to the ground state again.
There is a continuing need to develop new materials for the above-described organic light emitting devices.
Disclosure of Invention
Technical problem
The present specification is directed to providing compounds and organic electronic devices comprising the same.
Technical scheme
The present specification provides a compound represented by the following chemical formula 1.
[ chemical formula 1]
In the chemical formula 1, the first and second,
l is a direct bond, or a substituted or unsubstituted arylene group,
Ar1and Ar2Are the same or different from each other and are each independently hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl, or may combine with an adjacent group to form a ring,
R1to R9Are identical to or different from each other and are each independently hydrogen, deuterium, substituted or unsubstitutedOr a substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl group, or may be combined with an adjacent group to form a ring,
a is an integer of 1 to 4,
b is an integer of 1 to 5,
c is an integer of 1 to 3,
a + b is an integer of 2 to 8, and
when each of a to c is 2 or more, the structures in parentheses are the same as or different from each other.
Further, the present specification provides an organic electronic device comprising: a first electrode; a second electrode disposed to face the first electrode; and an organic material layer having one or more layers disposed between the first electrode and the second electrode, wherein one or more layers of the organic material layer contain the above compound.
Advantageous effects
The compound according to one exemplary embodiment of the present specification is used for an organic electronic device, including an organic light emitting device, and thus, due to thermal stability of the compound, it may reduce a driving voltage of the organic electronic device, improve light efficiency, and improve life span characteristics of the device.
Drawings
Fig. 1 illustrates an organic light emitting device 10 according to an exemplary embodiment of the present description.
Fig. 2 shows an organic light emitting device 11 according to another exemplary embodiment of the present description.
Description of the reference numerals
10. 11: organic light emitting device
20: substrate
30: a first electrode
40: luminescent layer
50: second electrode
60: hole injection layer
70: hole transport layer
80: electron blocking layer
90: electron transport layer
100: electron injection layer
EMBODIMENTS FOR CARRYING OUT THE INVENTION
Hereinafter, the present specification will be described in more detail.
The present specification provides a compound represented by chemical formula 1.
The compound of chemical formula 1 may have characteristics suitable for an organic material layer used in an organic light emitting device by introducing various substituents into a core structure.
The conjugation length and the energy band gap of the compounds are closely related to each other. Specifically, the longer the conjugation length of the compound, the smaller the band gap. As described above, the core of the compound represented by chemical formula 1 includes limited conjugation, and thus has a characteristic of large energy band gap.
In general, a substituent is introduced into a core structure having a large energy bandgap to easily adjust the energy bandgap, but when the core structure has a small energy bandgap, it is difficult to significantly adjust the energy bandgap by introducing the substituent. However, in the present specification, as described above, various substituents may be introduced into R of chemical formula 1 having a core structure with a large energy bandgap1To R9To synthesize compounds having various band gaps.
However, in the present specification, various substituents may be introduced into R of the core structure of the compound represented by chemical formula 11To R9The position to adjust the HOMO and LUMO levels of the compound, and also to improve the characteristics at the interface between organic materials, thereby diversifying the use of the material.
In addition, various substituents may be introduced into the core structure having the structure as described above to synthesize a compound having the inherent characteristics of the introduced substituents. For example, a substituent generally used in a hole injection layer material, a hole transport layer material, a light emitting layer material, and an electron transport layer material for manufacturing an organic light emitting device may be introduced into the core structure to synthesize a material satisfying conditions required for each organic material layer.
In the present specification, among the compounds represented by chemical formula 1, a compound having an appropriate energy level may be selected according to a substituent and used for an organic light emitting device, thereby realizing a device having a low driving voltage and high light efficiency. In addition, the energy band gap can be finely adjusted by introducing various substituents into the core structure, and at the same time, the characteristics at the interface between organic materials can be improved and the use of the materials can be diversified.
In addition, the compound represented by chemical formula 1 has a high glass transition temperature (Tg), and thus has excellent thermal stability. The improvement of thermal stability becomes an important factor for providing driving stability to the device.
Examples of the substituent in the present specification will be described below, but not limited thereto.
In the context of the present specification,
meaning the connected portions.
The term "substitution" means that a hydrogen atom bonded to a carbon atom of a compound is changed to another substituent, and the position of substitution is not limited as long as the position is a position at which the hydrogen atom is substituted (i.e., a position at which the substituent may be substituted), and when two or more are substituted, two or more substituents may be the same as or different from each other.
In the present specification, the term "substituted or unsubstituted" means substituted with one or two or more substituents selected from: deuterium, a halogen group, a cyano group, an amino group, an alkyl group, a cycloalkyl group, an alkenyl group, an amine group, a phosphinoxide group, an aryl group, a silyl group, and a heterocyclic group containing one or more of N, O, S, Se and Si atoms; substituted with a substituent attached to two or more of the exemplified substituents; or no substituent.
In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms thereof is not particularly limited, but is preferably 1 to 50. Specific examples thereof include methyl group, ethyl group, propyl group, n-propyl group, isopropyl group, butyl group, n-butyl group, isobutyl group, tert-butyl group, sec-butyl group, 1-methyl-butyl group, 1-ethyl-butyl group, pentyl group, n-pentyl group, isopentyl group, neopentyl group, tert-pentyl group, hexyl group, n-hexyl group, 1-methylpentyl group, 2-methylpentyl group, 4-methyl-2-pentyl group, 3-dimethylbutyl group, 2-ethylbutyl group, heptyl group, n-heptyl group, 1-methylhexyl group, cyclopentylmethyl group, cyclohexylmethyl group, octyl group, n-octyl group, tert-octyl group, 1-methylheptyl group, 2-ethylhexyl group, 2-propylpentyl group, n-nonyl group, 2-dimethylheptyl group, 1-ethyl-propyl group, 1-dimethyl-propyl group, 1, Isohexyl, 4-methylhexyl, 5-methylhexyl, and the like, but are not limited thereto.
In the present specification, the cycloalkyl group is not particularly limited, but the number of carbon atoms thereof is preferably 3 to 60, and specific examples thereof include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2, 3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2, 3-dimethylcyclohexyl, 3,4, 5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl and the like.
In the present specification, when the aryl group is a monocyclic aryl group, the number of carbon atoms thereof is not particularly limited, but is preferably 6 to 50. Specific examples of monocyclic aryl groups include phenyl, biphenyl, terphenyl, quaterphenyl, and the like, but are not limited thereto.
When the aryl group is a polycyclic aryl group, the number of carbon atoms thereof is not particularly limited, but is preferably 6 to 30. Specific examples of the polycyclic aryl group include naphthyl, anthryl, phenanthryl, pyrenyl, and the like,
A base,
A phenyl group, a fluorenyl group, and the like, but are not limited thereto.
In the present specification, the fluorenyl group may be substituted, and adjacent substituents may be bonded to each other to form a ring.
When the fluorenyl group is substituted, the group can be
And the like, but are not limited thereto.
In the present specification, the heteroaryl group is a heterocyclic group containing one or more of N, O, S, Si and Se as a heteroatom, and the number of carbon atoms thereof is not particularly limited, but is preferably 2 to 50. Examples of heteroaryl groups include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl,
Azolyl group,
Oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolyl, indolyl, carbazolyl, benzobenzoxazinyl
Azolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, benzofuranyl, phenanthrolinyl, isoquinoyl
Azolyl group,
Oxadiazolyl, thiadiazolyl, dibenzofuranyl, and the like, but is not limited thereto.
In the present specification, the fused structure may be a structure in which an aromatic hydrocarbon ring is fused with a corresponding substituent. Examples of fused rings of benzimidazoles include
And the like, but are not limited thereto.
In the present specification, an "adjacent" group may mean a substituent substituted with an atom directly connected to an atom substituted with the corresponding substituent, a substituent located sterically closest to the corresponding substituent, or another substituent substituted for an atom substituted with the corresponding substituent. For example, two substituents substituted at the ortho position on the phenyl ring and two substituents substituted for the same carbon on the aliphatic ring may be construed as groups "adjacent" to each other.
In the present specification, the case where adjacent groups are combined with each other to form a ring means that adjacent groups are combined with each other to form a 5-to 8-membered hydrocarbon ring or a 5-to 8-membered heterocyclic ring as described above, the ring may be monocyclic or polycyclic, and may be an aliphatic ring, an aromatic ring, or a condensed form thereof, but is not limited thereto.
In the present specification, the hydrocarbon ring or the heterocyclic ring may be selected from the above-mentioned examples of the cycloalkyl, aryl or heteroaryl group, except that it is a monovalent group, and the hydrocarbon ring or the heterocyclic ring may be a monocyclic or polycyclic, aliphatic or aromatic ring or a condensed form thereof, but is not limited thereto.
In this specification, an aromatic cyclic group may be monocyclic or polycyclic, and may be selected from examples of aryl groups, except for non-monovalent aromatic cyclic groups.
In the present specification, a divalent to tetravalent aromatic cyclic group may be monocyclic or polycyclic, and means a group having 2 to 4 binding positions in an aryl group, i.e., a divalent to tetravalent group. The above description of aryl groups applies to aromatic cyclic groups, except that these aromatic cyclic groups are divalent to tetravalent groups.
In the present specification, arylene means a group having two binding sites in an aryl group, that is, a divalent group. The above description for aryl groups applies to arylene groups, except that arylene groups are divalent groups.
In one exemplary embodiment of the present specification, chemical formula 1 may be represented by the following chemical formula 2 or 3.
[ chemical formula 2]
[ chemical formula 3]
In the chemical formulae 2 and 3,
L、Ar1、Ar2、R1to R9And a to c are the same as those defined in chemical formula 1.
In one exemplary embodiment of the present specification, chemical formula 1 may be represented by any one of the following chemical formulae 4 to 9.
[ chemical formula 4]
[ chemical formula 5]
[ chemical formula 6]
[ chemical formula 7]
[ chemical formula 8]
[ chemical formula 9]
In the chemical formulae 4 to 9,
L、Ar1、Ar2、R1to R9And a to c are the same as those defined in chemical formula 1.
In one exemplary embodiment of the present specification, L is a direct bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted phenanthrylene group, or a substituted or unsubstituted fluorenyl group.
In an exemplary embodiment of the present specification, L is a direct bond, or a phenylene group, a biphenylene group, a naphthylene group, a phenanthrene group, or a fluorenyl group.
In one exemplary embodiment of the present specification, L is phenylene.
In an exemplary embodiment of the present specification, L is biphenylene.
In an exemplary embodiment of the present specification, L is naphthylene.
In an exemplary embodiment of the present specification, L is a phenanthrylene group.
In one exemplary embodiment of the present specification, L is a divalent fluorenyl group.
In an exemplary embodiment of the present specification, Ar1And Ar2Are the same or different from each other, and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, or may be combined with an adjacent group to form a ring.
In an exemplary embodiment of the present specification, Ar1And Ar2Are the same or different from each other, and are each independently a substituted or unsubstituted aryl group having 2 to 30 carbon atoms.
In an exemplary embodiment of the present specification, Ar1And Ar2Are identical to or different from each other and are each independently substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstitutedSubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted triphenyl, substituted or unsubstituted phenanthryl, or substituted or unsubstituted fluorenyl.
In an exemplary embodiment of the present specification, Ar1And Ar2Are the same or different from each other, and are each independently a substituted or unsubstituted phenyl group, or may combine with an adjacent group to form a ring.
In an exemplary embodiment of the present specification, Ar1And Ar2Is phenyl.
In an exemplary embodiment of the present specification, Ar1And Ar2May be combined with an adjacent group to form a ring.
In an exemplary embodiment of the present specification, R1To R9Are the same or different from each other, and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, or may be combined with an adjacent group to form a ring.
In an exemplary embodiment of the present specification, R1To R9Are the same or different from each other, and are each independently a substituted or unsubstituted aryl group having 2 to 30 carbon atoms.
In an exemplary embodiment of the present specification, R1To R9The same or different from each other, and each independently is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted triphenyl group, a substituted or unsubstituted phenanthryl group, or a substituted or unsubstituted fluorenyl group.
In an exemplary embodiment of the present specification, R1To R9Are the same or different from each other, and are each independently a phenyl group.
In an exemplary embodiment of the present specification, R1To R9Are identical to each otherOr different and are each independently biphenyl.
In an exemplary embodiment of the present specification, R1To R9Are the same or different from each other, and are each independently a terphenyl group.
In an exemplary embodiment of the present specification, R1To R9Are the same or different from each other, and are each independently a naphthyl group.
In an exemplary embodiment of the present specification, R1To R9Are the same or different from each other, and are each independently a triphenyl group.
In an exemplary embodiment of the present specification, R1To R9Are the same or different from each other, and are each independently a phenanthryl group.
In an exemplary embodiment of the present specification, R1To R9Are the same or different from each other, and are each independently a fluorenyl group.
In an exemplary embodiment of the present specification, R1To R9Are identical to or different from one another and are each independently substituted or unsubstituted heteroaryl having from 6 to 30 carbon atoms.
In an exemplary embodiment of the present specification, R1To R9Are the same or different from each other, and are each independently a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidyl group, or a substituted or unsubstituted triazinyl group.
In an exemplary embodiment of the present specification, R1To R9Are the same or different from each other, and are each independently a pyridyl group.
In an exemplary embodiment of the present specification, R1To R9Are the same or different from each other, and are each independently a pyrimidinyl group.
In an exemplary embodiment of the present specification, R1To R9Are the same or different from each other, and are each independently a triazinyl group.
In an exemplary embodiment of the present descriptionIn, R1Is phenyl.
In an exemplary embodiment of the present specification, R1Is biphenyl.
In an exemplary embodiment of the present specification, R1Is a terphenyl group.
In an exemplary embodiment of the present specification, R1Is naphthyl.
In an exemplary embodiment of the present specification, R1Is triphenyl.
In an exemplary embodiment of the present specification, R1Is phenanthryl.
In an exemplary embodiment of the present specification, R1Is fluorenyl.
In an exemplary embodiment of the present specification, R1Is a pyridyl group.
In an exemplary embodiment of the present specification, R1Is a pyrimidinyl group.
In an exemplary embodiment of the present specification, R1Is a triazinyl group.
In an exemplary embodiment of the present specification, R2To R9Is hydrogen.
According to one exemplary embodiment of the present description, the compound may be any one selected from the following structural formulae:
compounds according to one exemplary embodiment of the present application may be prepared by the following preparative methods. Representative examples will be described in the following preparation examples, but substituents may be added or excluded, if necessary, and the positions of the substituents may be changed. Further, starting materials, reactants, reaction conditions, and the like may be varied based on techniques known in the art.
For example, the core structure of the compound of chemical formula 1 may be prepared as in the following general formulae 1 to 3. The substituents may be combined by a method known in the art, and the kind and position of the substituent or the number of the substituent may be changed according to a technique known in the art.
[ general formula 1]
2-aminophenyl-4-halophenyl-methanone and alkyl methyl ketone were placed in acetic acid at a concentration of 1M. In this case, a catalytic amount of sulfuric acid was simultaneously added thereto, and compound a was synthesized by refluxing the resulting mixture.
[ general formula 2]
Compound B is synthesized by performing a reaction of substituting a hydroxyl group with a leaving group after performing a coupling reaction of a fluoroboric acid derivative and a linking group derivative by using a palladium (Pd) catalyst.
[ general formula 3]
The same equivalent of compound a and compound B were mixed, and the structure of chemical formula 1 was synthesized by a coupling reaction using a palladium (Pd) catalyst.
In the general formulae 1 to 3, L, a to c, Ar1And Ar2And R1To R9The same as those described above.
In general formulae 1 to 3, examples of methods for synthesizing the core of chemical formula 1 are described, but the methods are not limited thereto.
Further, the present specification provides an organic electronic device comprising the above compound.
An exemplary embodiment of the present application provides an organic electronic device including: a first electrode; a second electrode disposed to face the first electrode; and an organic material layer having one or more layers disposed between the first electrode and the second electrode, wherein one or more layers of the organic material layer include the compound.
In this specification, when one member is disposed "on" another member, it includes not only a case where one member is brought into contact with another member but also a case where another member is present between the two members.
In the present specification, when a component "includes" one constituent element, it is not intended to exclude another constituent element unless specifically described otherwise, but is intended to include another constituent element as well.
The organic material layer of the organic electronic device of the present specification may also be composed of a single layer structure, and may be composed of a multilayer structure in which organic material layers having two or more layers are stacked. For example, as a representative example of the organic electronic device of the present invention, the organic light emitting device may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, an electron blocking layer, a hole blocking layer, and the like as organic material layers. However, the structure of the organic light emitting device is not limited thereto, and may include a smaller number of organic layers.
According to an exemplary embodiment of the present description, the organic electronic device may be selected from the group consisting of an organic phosphorescent device, an organic solar cell, an Organic Photoconductor (OPC), and an organic transistor.
In one exemplary embodiment of the present specification, the organic material layer includes a light emitting layer, and the light emitting layer includes the compound.
In one exemplary embodiment of the present specification, the organic material layer includes a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer includes the compound.
In one exemplary embodiment of the present specification, the organic material layer includes an electron injection layer, an electron transport layer, or a layer that simultaneously injects and transports electrons, and the electron injection layer, the electron transport layer, or the layer that simultaneously injects and transports electrons includes the compound.
In one exemplary embodiment of the present application, the organic material layer includes an electron blocking layer, and the electron blocking layer includes the compound.
In one exemplary embodiment of the present specification, the organic light emitting device further includes one or two or more layers selected from the group consisting of: a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, a hole blocking layer, and an electron blocking layer.
In one exemplary embodiment of the present specification, an organic light emitting device includes: a first electrode; a second electrode disposed to face the first electrode; a light-emitting layer provided between the first electrode and the second electrode; and an organic material layer including two or more layers, the organic material layer being disposed between the light emitting layer and the first electrode or between the light emitting layer and the second electrode, wherein at least one of the organic material layers including two or more layers contains the compound. In one exemplary embodiment of the present specification, as the organic material layer including two or more layers, two or more layers may be selected from an electron transport layer, an electron injection layer, a layer that simultaneously transports and injects electrons, and a hole blocking layer.
In one exemplary embodiment of the present specification, the organic material layer includes an electron transport layer having two or more layers, and at least one of the electron transport layers having two or more layers includes the compound. Specifically, in one exemplary embodiment of the present specification, the compound may be further included in one layer of electron transport layers including two or more layers, and may be included in each electron transport layer including two or more layers.
Further, in one exemplary embodiment of the present specification, when the compound is included in each electron transport layer including two or more layers, materials other than the compound may be the same as or different from each other.
In one exemplary embodiment of the present specification, the organic material layer includes a hole injection layer or a hole transport layer including a compound containing an arylamino group, a carbazolyl group, or a benzocarbazolyl group, in addition to the organic material layer including the compound.
In another exemplary embodiment, the organic light emitting device may be an organic light emitting device having a structure (normal type) in which: wherein a positive electrode, an organic material layer having one or more layers, and a negative electrode are sequentially stacked on a substrate.
When the organic material layer including the compound of chemical formula 1 is an electron transport layer, the electron transport layer may further include an n-type dopant. As the n-type dopant, those known in the art can be used, and for example, a metal or a metal complex can be used. According to one example, the electron transport layer including the compound of chemical formula 1 may further include LiQ.
In still another exemplary embodiment, the organic light emitting device may be an organic light emitting device having an inverted structure (inverted type) in which a negative electrode, an organic material layer having one or more layers, and a positive electrode are sequentially stacked on a substrate.
For example, the structure of the organic light emitting device of the present specification may have the structure as shown in fig. 1 and 2, but is not limited thereto.
Fig. 1 illustrates a structure of an organic light emitting device 10 in which a first electrode 30, a light emitting layer 40, and a second electrode 50 are sequentially stacked on a substrate 20. Fig. 1 is an exemplary structure of an organic light emitting device according to an exemplary embodiment of the present specification, and may further include other organic material layers.
Fig. 2 illustrates a structure of an organic light emitting device in which a first electrode 30, a hole injection layer 60, a hole transport layer 70, an electron blocking layer 80, a light emitting layer 40, an electron transport layer 90, an electron injection layer 100, and a second electrode 50 are sequentially stacked on a substrate 20. Fig. 2 is an exemplary structure according to some exemplary embodiments of the present description, and may further include other organic material layers.
According to one exemplary embodiment of the present specification, the organic material layer includes a light emitting layer, and the light emitting layer includes a compound represented by the following chemical formula 1-a.
[ chemical formula 1-A ]
In the chemical formula 1-a,
n1 is an integer of 1 or more,
ar11 is a substituted or unsubstituted monovalent or higher benzofluorenyl group, a substituted or unsubstituted monovalent or higher fluoranthenyl group, a substituted or unsubstituted monovalent or higher pyrenyl group, or a substituted or unsubstituted monovalent or higher pyrenyl group
The base group is a group of a compound,
l11 is a direct bond, a substituted or unsubstituted arylene, or a substituted or unsubstituted heteroarylene,
ar12 and Ar13 are the same as or different from each other and each independently is a substituted or unsubstituted aryl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted arylalkyl group, or a substituted or unsubstituted heteroaryl group, or may be combined with each other to form a substituted or unsubstituted ring, and
when n1 is 2 or more, the structures in two or more brackets are the same as or different from each other.
According to one exemplary embodiment of the present specification, the organic material layer includes a light emitting layer, and the light emitting layer includes a compound represented by chemical formula 1-a as a dopant of the light emitting layer.
According to an exemplary embodiment of the present description, L11 is a direct bond.
According to an exemplary embodiment of the present description, n1 is 2.
In one exemplary embodiment of the present specification, Ar11 is a divalent pyrenyl group that is unsubstituted or substituted with deuterium, methyl, ethyl, or tert-butyl; or divalent unsubstituted or substituted by deuterium, methyl, ethyl or tert-butyl
And (4) a base.
According to one exemplary embodiment of the present description, Ar12 and Ar13 are the same or different from each other and each independently is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
According to one exemplary embodiment of the present description, Ar12 and Ar13 are the same or different from each other and are each independently an aryl group that is unsubstituted or substituted with a silyl group substituted with a methyl group, an ethyl group, a tert-butyl group, a nitrile group, or an alkyl group.
According to one exemplary embodiment of the present description, Ar12 and Ar13 are the same or different from each other and each independently is an aryl group which is unsubstituted or substituted with a silyl group substituted with an alkyl group.
According to an exemplary embodiment of the present description, Ar12 and Ar13 are the same or different from each other and are each independently an unsubstituted or trimethylsilyl-substituted aryl group.
According to one exemplary embodiment of the present specification, Ar12 and Ar13 are the same or different from each other and are each independently a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, or a substituted or unsubstituted terphenyl.
According to an exemplary embodiment of the present description, Ar12 and Ar13 are the same or different from each other and are each independently phenyl unsubstituted or substituted with methyl, ethyl, tert-butyl, nitrile or trimethylsilyl.
According to an exemplary embodiment of the present description, Ar12 and Ar13 are the same or different from each other and are each independently biphenyl groups which are unsubstituted or substituted with methyl, ethyl, tert-butyl, nitrile or trimethylsilyl groups.
According to an exemplary embodiment of the present description, Ar12 and Ar13 are the same or different from each other and are each independently a terphenyl group that is unsubstituted or substituted with a methyl group, an ethyl group, a tert-butyl group, a nitrile group, or a trimethylsilyl group.
According to one exemplary embodiment of the present description, Ar12 and Ar13 are the same or different from each other and are each independently a substituted or unsubstituted heteroaryl group having 6 to 30 carbon atoms.
According to one exemplary embodiment of the present description, Ar12 and Ar13 are the same or different from each other and are each independently an unsubstituted or methyl, ethyl, tert-butyl, nitrile group, silyl substituted with alkyl, phenyl substituted heteroaryl.
According to an exemplary embodiment of the present description, Ar12 and Ar13 are the same or different from each other and are each independently an unsubstituted or methyl-, ethyl-, t-butyl-, nitrile-, trimethylsilyl-, or phenyl-substituted dibenzofuranyl group.
According to an exemplary embodiment of the present specification, chemical formula 1-a is selected from the following compounds.
According to one exemplary embodiment of the present specification, the organic material layer includes a light emitting layer, and the light emitting layer includes a compound represented by the following chemical formula 2-a.
[ chemical formula 2-A ]
In the chemical formula 2-a,
ar21 and Ar22 are the same or different from each other and are each independently a substituted or unsubstituted monocyclic aryl group or a substituted or unsubstituted polycyclic aryl group, and
g1 to G8 are the same or different from each other and are each independently hydrogen, substituted or unsubstituted monocyclic aryl, or substituted or unsubstituted polycyclic aryl.
According to one exemplary embodiment of the present specification, the organic material layer includes a light emitting layer, and the light emitting layer includes a compound represented by chemical formula 2-a as a host of the light emitting layer.
According to one exemplary embodiment of the present description, Ar21 and Ar22 are the same or different from each other and are each independently a substituted or unsubstituted polycyclic aryl group.
According to an exemplary embodiment of the present description, Ar21 and Ar22 are the same or different from each other and are each independently a substituted or unsubstituted polycyclic aryl group having 10 to 30 carbon atoms.
According to one exemplary embodiment of the present description, Ar21 and Ar22 are the same or different from each other and are each independently a substituted or unsubstituted naphthyl group.
According to one exemplary embodiment of the present specification, Ar21 and Ar22 are the same or different from each other and are each independently substituted or unsubstituted 1-naphthyl.
According to one exemplary embodiment of the present description, Ar21 and Ar22 are 1-naphthyl.
According to an exemplary embodiment of the present description, G1 to G8 are hydrogen.
According to an exemplary embodiment of the present specification, chemical formula 2-a is selected from the following compounds.
According to one exemplary embodiment of the present specification, the organic material layer includes a light emitting layer, and the light emitting layer includes a compound represented by chemical formula 1-a as a dopant of the light emitting layer and includes a compound represented by chemical formula 2-a as a host of the light emitting layer.
The organic light emitting device of the present specification can be manufactured by materials and methods known in the art, except that one or more of the organic material layers contains the compound of the present specification, i.e., the compound.
When the organic light emitting device includes a plurality of organic material layers, the organic material layers may be formed of the same material or different materials.
The organic light emitting device of the present specification may be manufactured by materials and methods known in the art, except that one or more layers of the organic material layers include the compound, i.e., the compound represented by chemical formula 1.
For example, the organic light emitting device of the present specification may be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate. In this case, the organic light emitting device may be manufactured by the following process: a metal or a metal oxide having conductivity or an alloy thereof is deposited on a substrate by using a Physical Vapor Deposition (PVD) method such as sputtering or electron beam evaporation to form a positive electrode, an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer is formed on the positive electrode, and then a material that can be used as a negative electrode is deposited on the organic material layer. In addition to the above-described method, the organic light emitting device may be manufactured by sequentially depositing a negative electrode material, an organic material layer, and a positive electrode material on a substrate.
In addition, the compound of chemical formula 1 may be formed into an organic material layer not only by a vacuum deposition method but also by a solution application method in manufacturing an organic light emitting device. Here, the solution application method means spin coating, dip coating, blade coating, inkjet printing, screen printing, spray coating, roll coating, and the like, but is not limited thereto.
In addition to the above-described methods, an organic light emitting device may be manufactured by sequentially depositing a negative electrode material, an organic material layer, and a positive electrode material on a substrate (international publication No. 2003/012890). However, the manufacturing method is not limited thereto.
In one exemplary embodiment of the present description, the first electrode is a positive electrode and the second electrode is a negative electrode.
In another exemplary embodiment of the present description, the first electrode is a negative electrode and the second electrode is a positive electrode.
As the positive electrode material, a material having a large work function is generally preferred to facilitate hole injection into the organic material layer. Specific examples of positive electrode materials that can be used in the present invention include: metals such as vanadium, chromium, copper, zinc and gold, or alloys thereof; metal oxides such as zinc oxide, Indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); combinations of metals and oxides, e.g. ZnO: Al or SnO2Sb; conducting polymers, e.g. poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene](PEDOT), polypyrrole, polyaniline, and the like, but are not limited thereto.
As the negative electrode material, a material having a small work function is generally preferred to facilitate electron injection into the organic material layer. Specific examples of the negative electrode material include: metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; materials of multilayer construction, e.g. LiF/Al or LiO2Al, etc., but are not limited thereto.
The hole injection layer is a layer that injects holes from the electrode, and the hole injection material is preferably a compound that has the ability to transport holes and thus has a hole injection effect at the positive electrode, to the light-emitting layer or the light-emitting materialHas an excellent hole injection effect, prevents excitons generated from the light emitting layer from moving to the electron injection layer or the electron injection material, and has an excellent thin film forming ability. Preferably, the Highest Occupied Molecular Orbital (HOMO) of the hole injection material is between the work function of the positive electrode material and the HOMO of the surrounding organic material layer. Specific examples of the hole injecting material include metalloporphyrin, oligothiophene, arylamine-based organic material, hexanenitrile-based hexaazatriphenylene-based organic material, quinacridone-based organic material, and quinacridone-based organic material
Organic materials, anthraquinones, polyaniline-based and polythiophene-based conductive polymers, and the like, but are not limited thereto.
The hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light emitting layer, and the hole transport material is suitably a material having high hole mobility, which can receive holes from the positive electrode or the hole injection layer and transport the holes to the light emitting layer. Specific examples thereof include arylamine-based organic materials, conductive polymers, block copolymers having both conjugated and non-conjugated portions, and the like, but are not limited thereto.
The electron blocking layer is a layer that can improve the lifetime and efficiency of the device by preventing holes injected from the hole injection layer from passing through the light emitting layer and entering the electron injection layer, and if necessary, can be formed at a suitable position between the light emitting layer and the electron injection layer using a known material.
The light-emitting material used for the light-emitting layer is a material which: which can emit light in the visible light range by receiving and combining holes and electrons from a hole transport layer and an electron transport layer, respectively, preferably a material having high quantum efficiency for fluorescence or phosphorescence. Specific examples thereof include: 8-hydroxy-quinoline-aluminum complex (Alq)3) (ii) a A carbazole-based compound; a di-polystyrene based compound; BAlq; 10-hydroxybenzoquinoline-metal compounds; based on benzene
Compounds of oxazole, benzothiazole and benzimidazole; polymers based on poly (p-phenylene vinylene) (PPV); a spiro compound; polyfluorene, rubrene, and the like, but are not limited thereto.
The light emitting layer may include a host material and a dopant material. Examples of the host material include a fused aromatic ring derivative, a heterocyclic ring-containing compound, or the like. Specific examples of the fused aromatic ring derivative include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like, and specific examples of the heterocycle-containing compounds include compounds, dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, and the like, but the examples are not limited thereto.
Examples of the dopant material include aromatic amine derivatives, styrene amine compounds, boron complexes, fluoranthene compounds, metal complexes, and the like. Specifically, the aromatic amine derivative is a condensed aromatic ring derivative having a substituted or unsubstituted arylamino group, and examples thereof include pyrene, anthracene, having an arylamino group,
Diindenopyrene, and the like; the styrylamine compound is a compound in which a substituted or unsubstituted arylamine is substituted with at least one arylvinyl group, and one or two or more substituents selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group, and an arylamino group are substituted or unsubstituted. Specific examples thereof include, but are not limited to, styrylamine, styrenediamine, styrenetriamine, styrenetetramine, and the like. Further, examples of the metal complex include iridium complexes, platinum complexes, and the like, but are not limited thereto.
The electron transport layer is a layer that receives electrons from the electron injection layer and transports the electrons to the light emitting layer, and the electron transport material is suitably a material having high electron mobility, which can efficiently receive electrons from the negative electrode and transport the electrons to the light emitting layer. Specific examples thereof include: al complex of 8-hydroxyquinoline comprising Alq3The complex of (A), an organic radical compound, a hydroxyflavone-metal complexAnd the like, but are not limited thereto. The electron transport layer may be used with any desired cathode material as used according to the related art. Suitable examples of cathode materials are in particular typical materials having a low work function, followed by an aluminum or silver layer. Specific examples thereof include cesium, barium, calcium, ytterbium and samarium, in each case followed by an aluminum or silver layer.
The electron injection layer is a layer that injects electrons from the electrode, and the electron injection material is preferably a compound of: it has an ability to transport electrons, has an effect of injecting electrons from a negative electrode, and an excellent effect of injecting electrons into a light-emitting layer or a light-emitting material, prevents excitons generated in the light-emitting layer from moving to a hole-injecting layer, and also has an excellent thin-film-forming ability. Specific examples thereof include fluorenones, anthraquinone dimethanes, diphenoquinones, thiopyran dioxides, and the like,
Azole,
Diazole, triazole, imidazole,
Tetracarboxylic acid, fluorenylidene methane, anthrone and the like and derivatives thereof, metal complex compounds, nitrogen-containing five-membered ring derivatives, and the like, but are not limited thereto.
Examples of the metal complex compounds include lithium 8-quinolinolato, zinc bis (8-quinolinolato), copper bis (8-quinolinolato), manganese bis (8-quinolinolato), aluminum tris (2-methyl-8-quinolinolato), gallium tris (8-quinolinolato), bis (10-hydroxybenzo [ h ] quinoline) beryllium, bis (10-hydroxybenzo [ h ] quinoline) zinc, bis (2-methyl-8-quinoline) gallium chloride, bis (2-methyl-8-quinoline) (o-cresol) gallium, bis (2-methyl-8-quinoline) (1-naphthol) aluminum, bis (2-methyl-8-quinoline) (2-naphthol) gallium, and the like, but are not limited thereto.
The hole-blocking layer is a layer that blocks holes from reaching the negative electrode, and may be formed generally under the same conditions as those of the hole-injecting layer. It is embodied in the form ofExamples include
Oxadiazole derivatives or triazole derivatives, phenanthroline derivatives, BCP, aluminum complexes, etc., but is not limited thereto.
The organic light emitting device according to the present specification may be a top emission type, a bottom emission type, or a dual emission type, depending on the material used.
In one exemplary embodiment of the present specification, the compound represented by chemical formula 1 may be included in an organic solar cell or an organic transistor, in addition to an organic light emitting device.
Based on similar principles to those applied to organic light emitting devices, the compounds according to the present description may even function in the following organic electronic devices: including organic phosphorescent devices, organic solar cells, organic photoconductors, organic transistors, and the like.
Detailed Description
Hereinafter, the present specification will be described in detail with reference to examples in order to specifically describe the specification. However, the embodiments according to the present specification may be modified in various forms, and it is not to be construed that the scope of the present specification is limited to the embodiments described in detail below. The embodiments of the present description are provided to more fully explain the present description to those of ordinary skill in the art.
< example >
< preparation example 1> -Synthesis of Compound 1
1) Synthesis of Compound 1-A
After (2-aminophenyl) (4-chlorophenyl) methanone (25.0g, 107.9mmol) and picoline (13.0g, 107.9mmol) were dissolved in 108ml of acetic acid under a nitrogen atmosphere, 3ml of anhydrous sulfuric acid was added thereto, and the resulting mixture was heated and stirred for 5 hours. The temperature was lowered to normal temperature, extraction was performed with chloroform, and the extract was washed with water. After removing moisture of the reaction product by anhydrous magnesium sulfate, the organic solvent was distilled and removed under reduced pressure, and the residue was washed with ethanol to prepare compound 1-a (27g, yield 79.0%).
MS[M+H]+＝317
2) Synthesis of Compound 1-B
Compound 1-A (25.0g, 78.9mmol), bis (pinacolato) diboron (22.0g, 86.8mmol) and potassium acetate (20.9g, 213.1mmol) were mixed under a nitrogen atmosphere and the resulting mixture was added to 100ml of bis
In an alkane, heated and stirred. Bis (dibenzylideneacetone) palladium (1.4g, 2.37mmol) and tricyclohexylphosphine (1.3g, 4.7mmol) were placed in the mixture while refluxing, and the resulting mixture was stirred for 8 hours while heating. After the reaction was terminated, the temperature was lowered to normal temperature, and then the mixture was filtered. The filtrate was added to water, extraction was performed with chloroform, and the organic layer was dried over anhydrous magnesium sulfate. The organic layer was distilled under reduced pressure and then washed with ethanol to prepare compound 1-B (27g, yield 84%).
MS[M+H]+＝409
3) Synthesis of Compound 1
After completely dissolving compound 1-B (20.0g, 49.0mmol) and 6- (9, 9-diphenyl-2-fluorenyl) -2-naphthyl-nonafluorobutane-1-sulfonate (36.4g, 49.0mmol) in tetrahydrofuran (50ml), 30ml of a 2M potassium carbonate aqueous solution was added thereto, and tetrakistriphenyl-phosphine palladium (1.7g, 1.5mmol) was placed therein, and the resulting mixture was stirred while heating for 4 hours. The temperature was lowered to normal temperature to terminate the reaction, and then the potassium carbonate solution was removed to filter the residue. The filtered solid was washed once with tetrahydrofuran and ethanol, respectively, to prepare compound 1(30.0g, yield: 85%).
MS[M+H]+＝725
< preparation example 2> -Synthesis of Compound 2
Compound 2 was prepared in the same manner as the preparation method of compound 1 except that 6- (9, 9' -spirobi [ fluorene ] -2-yl) naphthalen-2-yl 1,1,2,2,3,3,4,4, 4-nonafluorobutane-1-sulfonate was used instead of 6- (9, 9-diphenyl-2-fluorenyl) -2-naphthyl-nonafluorobutane-1-sulfonate.
MS[M+H]+＝723
< preparation example 3> -Synthesis of Compound 3
Compound 3 was prepared in the same manner as the preparation method of compound 1 except that 6- (9, 9-diphenyl-9H-fluoren-4-yl) naphthalen-2-yl 1,1,2,2,3,3,4,4, 4-nonafluorobutane-1-sulfonate was used instead of 6- (9, 9-diphenyl-2-fluorenyl) -2-naphthyl-nonafluorobutane-1-sulfonate.
MS[M+H]+＝725
< preparation example 4> -Synthesis of Compound 4
Compound 4 was prepared in the same manner as the preparation method of compound 1 except that 6- (9, 9' -spirobi [ fluorene ] -4-yl) naphthalen-2-yl 1,1,2,2,3,3,4,4, 4-nonafluorobutane-1-sulfonate was used instead of 6- (9, 9-diphenyl-2-fluorenyl) -2-naphthyl-nonafluorobutane-1-sulfonate.
MS[M+H]+＝723
< preparation example 5> -Synthesis of Compound 5
Compound 5 was prepared in the same manner as the preparation method of compound 1 except that 4- (9, 9-diphenyl-9H-fluoren-2-yl) phenyl 1,1,2,2,3,3,4,4, 4-nonafluorobutane-1-sulfonate was used instead of 6- (9, 9-diphenyl-2-fluorenyl) -2-naphthyl-nonafluorobutane-1-sulfonate.
MS[M+H]+＝675
< preparation example 6> -Synthesis of Compound 8
Compound 8 was prepared in the same manner as the preparation method of compound 1 except that 4- (9, 9' -spirobi [ fluorene ] -4-yl) phenyl 1,1,2,2,3,3,4,4, 4-nonafluorobutane-1-sulfonate was used instead of 6- (9, 9-diphenyl-2-fluorenyl) -2-naphthyl-nonafluorobutane-1-sulfonate.
MS[M+H]+＝673
< preparation example 7> -Synthesis of Compound 9
Compound 9 was prepared in the same manner as the preparation method of compound 1 except that 3- (9, 9-diphenyl-9H-fluoren-2-yl) phenyl 1,1,2,2,3,3,4,4, 4-nonafluorobutane-1-sulfonate was used instead of 6- (9, 9-diphenyl-2-fluorenyl) -2-naphthyl-nonafluorobutane-1-sulfonate.
MS[M+H]+＝675
< preparation example 8> -Synthesis of Compound 12
Compound 12 was prepared in the same manner as the preparation method of compound 1 except that 3- (9, 9' -spirobi [ fluorene ] -4-yl) phenyl 1,1,2,2,3,3,4,4, 4-nonafluorobutane-1-sulfonate was used instead of 6- (9, 9-diphenyl-2-fluorenyl) -2-naphthyl-nonafluorobutane-1-sulfonate.
MS[M+H]+＝673
< preparation example 9> -Synthesis of Compound 13
Compound 13 was prepared in the same manner as the preparation method of compound 1 except that 2- (9, 9-diphenyl-9H-fluoren-2-yl) phenyl-1, 1,2,2,3,3,4,4, 4-nonafluorobutane-1-sulfonate was used instead of 6- (9, 9-diphenyl-2-fluorenyl) -2-naphthyl-nonafluorobutane-1-sulfonate.
MS[M+H]+＝675
< preparation example 10> -Synthesis of Compound 17
Compound 17 was prepared in the same manner as the preparation method of compound 1 except that 7- (9, 9-diphenyl-9H-fluoren-2-yl) naphthalen-2-yl 1,1,2,2,3,3,4,4, 4-nonafluorobutane-1-sulfonate was used instead of 6- (9, 9-diphenyl-2-fluorenyl) -2-naphthyl-nonafluorobutane-1-sulfonate.
MS[M+H]+＝725
< preparation example 11> -Synthesis of Compound 18
Compound 18 was prepared in the same manner as the preparation method of compound 1 except that 7- (9, 9' -spirobi [ fluorene ] -2-yl) naphthalen-2-yl 1,1,2,2,3,3,4,4, 4-nonafluorobutane-1-sulfonate was used instead of 6- (9, 9-diphenyl-2-fluorenyl) -2-naphthyl-nonafluorobutane-1-sulfonate.
MS[M+H]+＝723
< preparation example 12> -Synthesis of Compound 21
1) Synthesis of Compound 21-A
Compound 21-a was prepared in the same manner as the preparation of compound 1-a, except that acetophenone was used instead of picoline.
MS[M+H]+＝316
2) Synthesis of Compound 21-B
Compound 21-B was prepared in the same manner as the preparation method of Compound 1-B except that [ Compound 21-A ] was used instead of [ Compound 1-A ].
MS[M+H]+＝408
3) Synthesis of Compound 21
Compound 21 was prepared in the same manner as the preparation of compound 17 except that compound 21-B was used instead of compound 1-B.
MS[M+H]+＝724
< preparation example 13> -Synthesis of Compound 22
Compound 22 was prepared in the same manner as the preparation method of compound 21 except that 7- (9, 9' -spirobi [ fluoren ] -2-yl) naphthalen-2-yl 1,1,2,2,3,3,4,4, 4-nonafluorobutane-1-sulfonate was used instead of 7- (9, 9-diphenyl-9H-fluoren-2-yl) naphthalen-2-yl 1,1,2,2,3,3,4,4, 4-nonafluorobutane-1-sulfonate.
MS[M+H]+＝722
< preparation example 14> -Synthesis of Compound 25
Compound 25 was prepared in the same manner as the preparation method of compound 1 except that 4- (9, 9-diphenyl-9H-fluoren-2-yl) naphthalen-1-yl 1,1,2,2,3,3,4,4, 4-nonafluorobutane-1-sulfonate was used instead of 6- (9, 9-diphenyl-2-fluorenyl) -2-naphthyl-nonafluorobutane-1-sulfonate.
MS[M+H]+=725
< preparation example 15> -Synthesis of Compound 33
Compound 33 was prepared in the same manner as the preparation method of compound 1 except that 7- (9, 9-diphenyl-9H-fluoren-2-yl) phenanthren-2-yl 1,1,2,2,3,3,4,4, 4-nonafluorobutane-1-sulfonate was used instead of 6- (9, 9-diphenyl-2-fluorenyl) -2-naphthyl-nonafluorobutane-1-sulfonate.
MS[M+H]+＝775
< preparation example 16> -Synthesis of Compound 34
Compound 34 was prepared in the same manner as the preparation method of compound 1 except that 7- (9, 9' -spirobi [ fluorene ] -2-yl) phenanthren-2-yl 1,1,2,2,3,3,4,4, 4-nonafluorobutane-1-sulfonate was used instead of 6- (9, 9-diphenyl-2-fluorenyl) -2-naphthyl-nonafluorobutane-1-sulfonate.
MS[M+H]+＝773
< preparation example 17> -Synthesis of Compound 45
1) Synthesis of Compound 45-A
Compound 45-A was prepared in the same manner as the preparation of compound 1-A except that (2-amino-4-chlorophenyl) (phenyl) methanone was used instead of 2-aminophenyl-4-chlorophenyl methanone.
MS[M+H]+＝317
2) Synthesis of Compound 45-B
Compound 45-B was prepared in the same manner as the preparation method of Compound 1-B except that [ Compound 45-A ] was used instead of [ Compound 1-A ].
MS[M+H]+＝409
3) Synthesis of Compound 45
Compound 45 was prepared in the same manner as the preparation method of compound 1 except that [ compound 45-B ] was used instead of [ compound 1-B ], and 4- (9, 9-diphenyl-9H-fluoren-2-yl) phenyl 1,1,2,2,3,3,4,4, 4-nonafluorobutane-1-sulfonate was used instead of 6- (9, 9-diphenyl-2-fluorenyl) -2-naphthyl-nonafluorobutane-1-sulfonate.
MS[M+H]+＝675
< preparation example 18> -Synthesis of Compound 57
Compound 57 was prepared in the same manner as the preparation method of compound 1 except that [ compound 45-B ] was used instead of [ compound 1-B ], and 7- (9, 9-diphenyl-9H-fluoren-2-yl) naphthalen-2-yl 1,1,2,2,3,3,4,4, 4-nonafluorobutane-1-sulfonate was used instead of 6- (9, 9-diphenyl-2-fluorenyl) -2-naphthyl-nonafluorobutane-1-sulfonate.
MS[M+H]+＝725
< example >
< example 1>
Thinly coated with a thickness of
The glass substrate (Corning glass) of ITO (indium tin oxide) of (1) was put in distilled water in which a dispersant was dissolved, and ultrasonic washing was performed. The product manufactured by Fischer co. was used as a cleaning agent, and distilled water filtered twice using a filter manufactured by Millipore co. was used as distilled water. After washing ITO for 30 minutes, ultrasonic washing was repeated twice for 10 minutes using distilled water. After completion of washing with distilled water, ultrasonic washing was performed using isopropyl alcohol, acetone, and methanol solvents in this order, followed by drying.
Reacting hexacyano hexaazatriphenylene with
Is thermally vacuum-deposited on the transparent ITO electrode thus prepared, thereby forming a hole injection layer. Vacuum depositing hole transporting material HT1 thereon
Then vacuum depositing a host H1 compound and a dopant D1 compound as a light emitting layer to
Is measured. The compound 1 prepared in preparation example 1 and LiQ (lithium quinolate) were vacuum-deposited on the light emitting layer at a weight ratio of 1:1, thereby forming a layer having a thickness of
Electron injection and transport layers.
On the electron injection and transport layers, respectively
And
lithium fluoride (LiF) and aluminum are sequentially deposited to thereby form a negative electrode. An organic light emitting device is manufactured.
In the above step, the deposition rate of the organic material is maintained at
Second to
Per second, the deposition rates of lithium fluoride and aluminum of the negative electrode are respectively maintained at
Second and
second, and the degree of vacuum during deposition was maintained at 2X 10-7Hold in the palm to 5 x 10-6And thus an organic light emitting device was manufactured.
< example 2>
An experiment was performed in the same manner as in example 1 except that compound 2 was used instead of compound 1 as an electron injecting and transporting layer.
< example 3>
An experiment was performed in the same manner as in example 1 except that compound 3 was used instead of compound 1 as an electron injecting and transporting layer.
< example 4>
An experiment was performed in the same manner as in example 1 except that compound 4 was used instead of compound 1 as an electron injecting and transporting layer.
< example 5>
An experiment was performed in the same manner as in example 1 except that compound 5 was used instead of compound 1 as an electron injecting and transporting layer.
< example 6>
An experiment was performed in the same manner as in example 1 except that compound 8 was used instead of compound 1 as an electron injecting and transporting layer.
< example 7>
An experiment was performed in the same manner as in example 1 except that compound 9 was used instead of compound 1 as an electron injecting and transporting layer.
< example 8>
An experiment was performed in the same manner as in example 1 except that compound 12 was used instead of compound 1 as an electron injecting and transporting layer.
< example 9>
An experiment was performed in the same manner as in example 1 except that compound 13 was used instead of compound 1 as an electron injecting and transporting layer.
< example 10>
An experiment was performed in the same manner as in example 1 except that compound 17 was used instead of compound 1 as an electron injecting and transporting layer.
< example 11>
An experiment was performed in the same manner as in example 1 except that compound 18 was used instead of compound 1 as an electron injecting and transporting layer.
< example 12>
An experiment was performed in the same manner as in example 1 except that compound 21 was used instead of compound 1 as an electron injecting and transporting layer.
< example 13>
An experiment was performed in the same manner as in example 1 except that compound 22 was used instead of compound 1 as an electron injecting and transporting layer.
< example 14>
An experiment was performed in the same manner as in example 1 except that compound 25 was used instead of compound 1 as an electron injecting and transporting layer.
< example 15>
An experiment was performed in the same manner as in example 1 except that compound 33 was used instead of compound 1 as an electron injecting and transporting layer.
< example 16>
An experiment was performed in the same manner as in example 1 except that compound 34 was used instead of compound 1 as an electron injecting and transporting layer.
< example 17>
An experiment was performed in the same manner as in example 1 except that compound 45 was used instead of compound 1 as an electron injecting and transporting layer.
< example 18>
An experiment was performed in the same manner as in example 1 except that compound 57 was used instead of compound 1 as an electron injecting and transporting layer.
< comparative example 1>
An experiment was performed in the same manner as in example 1 except that as the electron injecting and transporting layer, the following compound ET1 was used instead of compound 1.
[ET1]
< comparative example 2>
An experiment was performed in the same manner as in example 1 except that as the electron injecting and transporting layer, the following compound ET2 was used instead of compound 1.
[ET2]
When a current was applied to the organic light emitting devices manufactured in examples 1 to 18 and comparative examples 1 to 2, the results of table 1 below were obtained.
[ Table 1]
As shown in table 1, it can be seen that the organic light emitting device manufactured by using the compound represented by chemical formula 1 of the present specification as an electron injection and transport layer exhibits excellent characteristics in terms of efficiency, driving voltage, and/or stability of the organic light emitting device.
Specifically, it can be confirmed that the compound having the structure represented by chemical formula 1 of the present specification has more improved voltage, efficiency and lifespan characteristics as compared to the existing electron transport layer material in comparative example 1, and that the aromatic or fused-fluorene structure of the compound represented by chemical formula 1 has more improved low voltage characteristics and efficiency characteristics through electron-rich material characteristics and shows more heat-stable characteristics as compared to the organic light emitting device of comparative example 2 manufactured by using the compound having an alkyl-fluorene structure as an electron injection and transport layer.
Although some preferred exemplary embodiments of the present invention (electron injection and transport layer) have been described above, the present invention is not limited thereto, and various modifications may be made and made within the scope of the claims and the detailed description of the present invention, and these modifications also fall within the scope of the present invention.
Claims (14)
1. A compound represented by any one of the following chemical formulas 4,5 and 8:
[ chemical formula 4]
[ chemical formula 5]
[ chemical formula 8]
In chemical formulas 4,5 and 8,
l is a direct bond, phenylene, biphenylene, naphthylene, divalent phenanthrene, or divalent fluorenyl,
Ar1and Ar2Identical to or different from each other and each independently is phenyl, or optionally in combination with adjacent groups to form a 5-to 8-membered aromatic ring or a fused form thereof,
R1is phenyl, biphenyl, naphthyl, phenanthryl, or pyridyl,
R2to R9Are the same or different from each other and are each independently hydrogen, deuterium, an alkyl group having 1 to 50 carbon atoms, a cycloalkyl group having 3 to 60 carbon atoms, a monocyclic aryl group having 6 to 50 carbon atoms, a polycyclic aryl group having 6 to 30 carbon atoms, or a heteroaryl group having 2 to 50 carbon atoms, a is an integer of 1 to 4,
b is an integer of 1 to 5,
c is an integer of 1 to 3,
a + b is an integer of 2 to 8, and
when each of a to c is 2 or more, the structures in parentheses are the same as or different from each other.
2. The compound according to claim 1, selected from the following compounds:
3. an organic electronic device comprising:
a first electrode;
a second electrode disposed to face the first electrode; and
an organic material layer having one or more layers disposed between the first electrode and the second electrode,
wherein one or more of the layers of organic material comprise a compound of any one of claims 1 to 2.
4. The organic electronic device according to claim 3, wherein the organic material layer comprises a light-emitting layer, and the light-emitting layer contains the compound.
5. The organic electronic device according to claim 3, wherein the organic material layer comprises a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer contains the compound.
6. The organic electronic device according to claim 3, wherein the organic material layer comprises an electron injection layer, an electron transport layer, or a layer that simultaneously injects and transports electrons, and the electron injection layer, the electron transport layer, or the layer that simultaneously injects and transports electrons contains the compound.
7. The organic electronic device according to claim 3, wherein the organic material layer comprises an electron blocking layer or a hole blocking layer, and the electron blocking layer or the hole blocking layer contains the compound.
8. The organic electronic device of claim 3, wherein the organic electronic device further comprises one or two or more layers selected from a light emitting layer, a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, an electron blocking layer, and a hole blocking layer.
9. The organic electronic device according to claim 3, wherein the organic electronic device is selected from the group consisting of organic light emitting devices, organic phosphorescent devices, organic solar cells, organic photoconductors, and organic transistors.
10. The organic electronic device according to claim 3, wherein the organic material layer comprises a light emitting layer, and the light emitting layer contains a compound represented by the following chemical formula 1-A:
[ chemical formula 1-A ]
In the chemical formula 1-a,
n1 is an integer of 1 or more,
ar11 is a substituted or unsubstituted monovalent or higher benzofluorenyl group, a substituted or unsubstituted monovalent or higher fluoranthenyl group, a substituted or unsubstituted monovalent or higher pyrenyl group, or a substituted or unsubstituted monovalent or higher pyrenyl group
The base group is a group of a compound,
l11 is a direct bond, a substituted or unsubstituted arylene, or a substituted or unsubstituted heteroarylene,
ar12 and Ar13 are the same or different from each other and are each independently a substituted or unsubstituted aryl, substituted or unsubstituted silyl, substituted or unsubstituted alkyl, substituted or unsubstituted arylalkyl, or substituted or unsubstituted heteroaryl group, or are optionally combined with each other to form a substituted or unsubstituted ring, and
when n1 is 2 or more, the structures in two or more brackets are the same as or different from each other.
11. The organic electronic device according to claim 10, wherein L11 is a direct bond, Ar11 is a divalent pyrenyl group, Ar12 and Ar13 are the same or different from each other and are each independently an aryl group that is unsubstituted or substituted with a silyl group substituted with an alkyl group, and n1 is 2.
12. The organic electronic device according to claim 3, wherein the organic material layer comprises a light emitting layer, and the light emitting layer contains a compound represented by the following chemical formula 2-A:
[ chemical formula 2-A ]
In the chemical formula 2-a,
ar21 and Ar22 are the same or different from each other and are each independently a substituted or unsubstituted monocyclic aryl group or a substituted or unsubstituted polycyclic aryl group, and
g1 to G8 are the same or different from each other and are each independently hydrogen, substituted or unsubstituted monocyclic aryl, or substituted or unsubstituted polycyclic aryl.
13. The organic electronic device of claim 12, wherein Ar21 and Ar22 are 1-naphthyl, and G1 to G8 are hydrogen.
14. The organic electronic device according to claim 10, wherein the light emitting layer comprises a compound represented by the following chemical formula 2-a:
[ chemical formula 2-A ]
In the chemical formula 2-a,
ar21 and Ar22 are the same or different from each other and are each independently a substituted or unsubstituted monocyclic aryl group or a substituted or unsubstituted polycyclic aryl group, and
g1 to G8 are the same or different from each other and are each independently hydrogen, substituted or unsubstituted monocyclic aryl, or substituted or unsubstituted polycyclic aryl.
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